Genotoxic activity of important nitrobenzenes and nitroanilines in the Ames test and their structure-activity relationship.
The most important commercially available nitro- and aminobenzenes and the explosive trinitrobenzene were tested for mutagenicity in the Salmonella typhymurium TA 98 and TA 100 both in the absence and presence of S 9. Ten of the 14 compounds tested (71%) were mutagenic. All the substances showed positive results in TA 98 and 4 substances were also mutagenic in TA 100. The three diaminobenzenes and 4-nitroaniline were mutagenic only with metabolic activation. All other compounds did not require the addition of S 9. Only nitrobenzene, 1,2-dinitrobenzene, aniline and 2-nitroaniline were negative in both strains. In summary, all substances that are derived from nitrobenzene or aniline by addition of a nitro group in the meta- or para-position were mutagenic, whereas nitrobenzene and aniline themselves and their ortho-derivates were nonmutagenic. The possible relationships between the position of the substituents and the mutagenicity are discussed.
Assmann
N
N
Institute for Hygiene, Environmental and Occupational Medicine, Free University of Berlin, Germany.
Emmrich
M
M
Kampf
G
G
Kaiser
M
M
D000814:Aniline Compounds / Q000737:chemistry* / Q000633:toxicity*; D000818:Animals; D008297:Male; D008862:Microsomes, Liver / Q000378:metabolism; D009152:Mutagenicity Tests; D009153:Mutagens / Q000737:chemistry / Q000633:toxicity*; D009578:Nitrobenzenes / Q000737:chemistry* / Q000633:toxicity*; D051381:Rats; D017207:Rats, Sprague-Dawley; D012486:Salmonella typhimurium / Q000187:drug effects / Q000235:genetics; D013329:Structure-Activity Relationship
D000814:Aniline Compounds; D009153:Mutagens; D009578:Nitrobenzenes; C008625:nitroaniline